Hydrochloric Acid → HCID 44447720, compound

HRID 1866855Notes

Reaction equation

[C:1]1([C:7]2([C:14]3[CH:23]=[C:22]([O:24][CH2:25][C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[CH:21]=[CH:20][C:15]=3[C:16]([O:18]C)=[O:17])[CH2:12][CH:11]3[CH2:13][CH:8]2[CH2:9][CH2:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Cl>C1COCC1.C(O)C(O)C.O>[C:1]1([C:7]2([C:14]3[CH:23]=[C:22]([O:24][CH2:25][C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[CH:21]=[CH:20][C:15]=3[C:16]([OH:18])=[O:17])[CH2:12][CH:11]3[CH2:13][CH:8]2[CH2:9][CH2:10]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 2b (67.0 mg, 0.14 mmol) in THF (3 mL) and 1,2-propanediol (3 mL) was added aqueous potassium hydroxide (0.40 mL of a 8 M solution in water, 3.20 mmol). The mixture was stirred at 110° C. for 18 h and then cooled to room temperature. The reaction mixture was diluted with water, acidified with 1 N hydrochloric acid and extracted three times with EtOAc. The combined organic extracts were washed with water, dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel; dichloromethane/methanol/concentrated aqueous ammonium hydroxide (85:15:1) gave a solid (48.0 mg) that was triturated with ether/hexane to provide 2c as a solid (38 mg), m.p. 205-210° C. (dec.).

Workup

temperaturecooled to room temperature
extractionextracted three times with EtOAc
washThe combined organic extracts were washed with water
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-3133dbd6693f43f0a433753d452ac0a1
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629467B2

Reaction notes

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